Sailing Lessons in the Hamptons 

Thinking about sailing lessons in the Hamptons? Start where the water is calm. Sag Harbor Sailing teaches on the sheltered back bays of the East End, not the open Sound or ocean. The bays are protected, the wind is steadier, and the scenery is hard to beat. That makes your first day on the water easier and a lot less stressful. We have taught beginners and returning sailors here since 1997. Whatever brings you aboard, you can learn to sail in the Hamptons at your own pace.

There is more than one way to learn with us. Pick the path that fits how you like to learn.

Our School and Our Approach

Private lessons give you the captain's full attention. You set the pace and the focus. Want to spend the whole session on docking? Done. Nervous about the boat heeling in a breeze? We ease into it. Each session takes up to four students, so you can come solo or bring up to three friends or family. See our private sailing lessons for details and booking.

Group classes run three times a day through the season. They are a friendly, lower-cost way to learn alongside others. Each class takes up to four students. You still get plenty of hands-on time at the helm, not just a turn watching.

The ASA 101 course is our two-day certification. It runs Thursday and Friday or Saturday and Sunday, from June through September. Pass it and you are certified to skipper a 23-foot keelboat in light to moderate winds. The course mixes shore-side basics with real time at the helm. You cover knots, points of sail, the rules of the road, and crew-overboard recovery. After you pass, you can charter a 23-foot keelboat on your own or with friends. Many students take a private lesson first to build confidence. Learn more about the ASA 101 certification course. 

So what does a lesson actually look like?

You sail a 23-foot Pearson Ensign, a stable keelboat that is forgiving and easy to read. Your instructor is licensed by the U.S. Coast Guard, and most have more than 20 years on the water. Because the group is small, no one waits their turn. You are on the helm, trimming sails, and getting feedback as you go. Every lesson includes life jackets and safety gear. You just bring sunscreen, a hat, and soft-soled shoes.

Sessions run about three hours. Slots are 9:00 to 12:00, 12:30 to 3:30, and 4:00 to 7:00. Depending on your level, your time on the water can cover the parts of the boat, reading the wind, steering, tacking and jibing, sail trim, and safe docking. Beginners usually leave their first time out having steered the boat and sailed a few legs on their own.

Who Learns With Us

These lessons are for almost anyone. We teach total first-timers and sailors shaking off the rust. Students from age 8 to 80 and up have learned here. Couples, families, and groups all sail with us. Companies book us too, including Fortune 500 teams for sailing regattas. We also run lessons for special occasions, like a birthday or an anniversary out on the water. Younger sailors have their own track in our youth summer sailing program for ages 9 to 16. 

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Why Learn With Us

Here is how pricing works. Lessons start at $475 plus fuel, staff and gratuity. That add-on covers your captain and the boat's running costs, so ask for your all-in total when you book. Call (631) 725-5100 for current lesson and ASA 101 certification rates. If you plan to sail often, our Commodores Club can lower your per-trip cost for the season.

Most people follow a simple path with us. Start with a lesson. Earn your ASA 101. Rent a boat. Then sail all season as a Commodores Club member. You can jump in at any step that fits your skills.

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Sailing School in the Hamptons

Why learn here instead of somewhere else? A few reasons. As an ASA-accredited sailing school, we follow a proven national curriculum. Our captains are USCG-licensed with decades of experience. We have run this school since 1997, with hundreds of ASA 101 graduates. And the protected bays make a gentler classroom than open water. Once you are certified, you can rent a sailboat and keep building your skills.

We sail out of the Yacht Hampton Boating Center at 51 Pine Neck Avenue in Sag Harbor, from mid-May right through the end of September. Ready to get out on the water? Book your lesson online or call (631) 725-5100. Summer dates fill fast, so reserve ahead.

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Lessons & Classes

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Private Sailing Lessons

Location Sag Harbor
$475 + Fuel, Staff & Gratuity
Length 23
Capacity 4
Crew 1 Captain
Bathroom(s) 1
Trip Type Day
More Info
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American Sailing Association Certification Course Image 1
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American Sailing Association Certification Course

Location Sag Harbor
$990 + Fuel, Staff & Gratuity
Length 23
Capacity 4
Crew 1 Captain
Bathroom(s) 1
Trip Type Day
More Info

All boats will be captained by a USCG licensed captain.

Hours & Pricing

Morning Session, 9:00 am–12:00 pm: $1,500 per week or $500 per day

Sessions runs from Monday, July 1 through August 30, 2024

$40 gratuity for counselors & crew are included in registration checkout.

 

FAQs

NEED AN ESCAPE?

Lets have a fun and memorable day!

Ready to Learn to Sail?

You don’t need experience, your own boat, or a free week. You just need a willingness to get out on the water. Pick a group lesson, a private session, or a full ASA course, and we’ll handle the rest. Call or text us at (631) 725-5100 with a question, or to book your first lesson. We’d love to teach you to sail.